Acrylonitrile → 4-Cyano-2-diaminomethylene-butyric acid ethyl ester

HRID 2079945Notes

Reaction equation

HRID 2079945 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:10])[CH:6]=[C:7]([NH2:9])[NH2:8])[CH3:3].C(N(CC)CC)C.[C:18](#[N:21])[CH:19]=[CH2:20]>O1CCCC1>[CH2:2]([O:4][C:5](=[O:10])[C:6]([CH2:20][CH2:19][C:18]#[N:21])=[C:7]([NH2:9])[NH2:8])[CH3:3]

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 8471TriethylamineHCID 124946853,3-Diamino-acrylic acid ethyl ester hydrochloride

Product 1

HCID 124949064-Cyano-2-diaminomethylene-butyric acid ethyl esterYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The resulting 3,3-diamino-acrylic acid ethyl ester hydrochloride (2.2 g, 13.2 mmol) was suspended in tetrahydrofuran (40 mL), triethylamine (2 mL, 14.3 mmol) and acrylonitrile (1.2 mL, 19.3 mmol) were added thereto, and the solution was refluxed for 6 hours. After the reaction was completed, the resulting triethylamine hydrochloride was filtered, and the filtrate was concentrated to obtain the title compound (0.6 g, 3.3 mmol, 25%).

Workup

  1. temperaturethe solution was refluxed for 6 hours
  2. filtrationthe resulting triethylamine hydrochloride was filtered
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-c7c9ccec28754008a4a0fb919cbcca90
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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